JP2001131436A - Water insoluble monoazo dye - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide blue-series disperse dyes which have good dischargeability and, at the same time, excellent dyeability, sublimation fastness and, washing fastness, and, in addition, excellent build-up. SOLUTION: The blue-series disperse dyes are water insoluble monoazo dyes represented by the formula (wherein R1 is a hydrogen atom, a methoxy group or an ethoxy group; R2 is a 1-6C alkylsulfonyl group; and R3 and R4 are each independently a 1-6C alkyl group, a 1-6C alkoxy-carbonylethyl group, a 1-6C alkoxy-ethyl group, a cyanoethyl group or an allyl group, provided that R2 can be a 1-6C alkyl-carbonyl group when any one of R3 and R4 is an allyl group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a novel water-insoluble monoazo dye, and more particularly, to an excellent leveling property, light fastness, sublimation fastness, washing fastness and build-up property, and good dischargeability. And a water-insoluble monoazo dye. Furthermore, the present invention relates to a method for dyeing or printing a fiber material using the monoazo dye, and a fiber material dyed or printed in this way.

[0002]

2. Description of the Related Art In recent years, with the trend toward fashion, luxury, and high added value, a dyeing / discharging method has been adopted as a dyeing technique. The feature of this method is that the printed pattern can be expressed clearly and delicately. As the blue dye used for discharge dyeing adopted in this method, the Color Index Nu
mber Disperse B-106 (hereinafter abbreviated as B-106) is used.

However, B-106 is not sufficient in terms of fastness, and is developed with a dischargeable blue dye which has good dyeability and excellent fastnesses, especially, sublimation fastness and washing fastness. Is strongly demanded by the industry.

[0004]

DISCLOSURE OF THE INVENTION The present invention provides a blue disperse dye having not only good discharge properties but also excellent dyeability, sublimation fastness and washing fastness, and excellent build-up properties. The purpose is to do so. It is a further object of the present invention to provide a method for dyeing or printing fiber materials and an improved dyeing or printing fiber material which is improved by using this dye.

[0005]

Means for Solving the Problems The gist of the present invention is the following general formula [1]:

[0006]

Embedded image (R ₁ represents a hydrogen atom, a methoxy group or an ethoxy group, R ₂ represents a C ₁ to C ₆ , preferably a C _{1 to} C ₄ alkylsulfonyl group, and R ₃ and R ₄ are each independently C ₁ -C ₆ , preferably C ₁ -C ₄ alkyl, C ₁ -C _6- , preferably C ₁ -C ₄ -alkoxy-
A carbonylethyl group, C ₁ to C _6- , preferably C ₁ to
Represents a C ₄ -alkoxy-ethyl group, a cyanoethyl group or an allyl group, provided that when at least one of R ₃ and R ₄ is an allyl group, R ₂ is from C ₁ to C _6- , preferably C _{1 to} C
₄ -alkyl-carbonyl group).

The alkyl in the alkylsulfonyl group and the alkylcarbonyl group as the group R ² and the groups R ₃ and R ₄
Alkyl may be linear or branched, for example, methyl, ethyl, n-propyl, isopropyl, n-, se
c-, iso- or tert-butyl, particularly preferably methyl and ethyl groups. The same applies to the alkoxycarbonylethyl groups as groups R ₃ and R ₄ and the alkyl part of the alkoxy in the alkoxyethyl groups. The substituents R _{1 to} R ₄ may be substituted with any substituent, as long as it does not substantially affect the dyeing effect achieved by the present invention. Therefore, the substituents R ₁ to
Dyes of the formula [1] with R ₄ can additionally be considered to be within the scope of the present invention.

The azo dye represented by the general formula [1] is
2-Amino-6-nitrobenzothiazole is diazotized by a conventional method to give a compound of the general formula [2]

[0009]

Embedded image (Wherein, R ₁ , R ₂ , R ₃ and R ₄ represent the above-mentioned meanings), and can be easily produced by coupling.

[0010] Examples of the coupling component represented by the general formula [2] include the following compounds.

N-ethyl, N-cyanoethyl-2-methoxy-5-methylsulfonylaminoaniline, N, N-
Dimethoxyethyl-2-methoxy-5-methylsulfonylaminoaniline, N, N-diethyl-2-methoxy-
5-methylsulfonylaminoaniline, N, N-diallyl-2-methoxy-5-methylsulfonylaminoaniline, N, N-diethyl-3-methylsulfonylaminoaniline, N, N-diallyl-2-methoxy-5-acetyl Aminoaniline The fiber material that can be dyed with the azo dye of the present invention is not particularly limited as long as it can be dyed with a disperse dye, but polyethylene terephthalate, terephthalic acid, 1,4-bis- (hydroxymethyl) cyclohexane and And hydrophobic fibers such as a blend of natural fibers such as cotton, silk, wool, or the like, or synthetic fibers such as nylon and the above-mentioned polyester fibers.

In carrying out the dyeing using the dye of the present invention, a dispersant is used in a conventional manner, and
The azo dye represented by the formula [1] may be dispersed in an aqueous medium to prepare a dyeing bath or printing paste, and then the ink may be dyed or printed.

For example, in the case of dyeing, a polyester fiber or a blend thereof or a blend thereof is excellent in fastness by applying a usual dyeing method such as a high temperature dyeing method, a carrier dyeing method or a thermosol dyeing method. Can be dyed.

The dyed fabric obtained by the above-described dyeing or printing using the azo dye of the present invention has excellent fastness and dischargeability,
By performing the discharge printing treatment, a clear, delicate and excellent dyeing pattern can be obtained.

Therefore, the present invention provides a method for dyeing or printing a fiber material using the dye of the above formula [1] according to the present invention, and in particular, dyeing or printing the fiber material using this dye, and then performing a discharge treatment. The present invention also provides a method for dyeing a fiber material, which is characterized by performing the following, and a fiber material dyed or printed in this way.

The discharge dyeing treatment is carried out by applying a bleaching chemical to the dyed fabric and post-treating the same, as is usual. As the discharge printing method, any of white discharge, colored discharge and semi-discharge methods can be advantageously selected.

The azo dye according to the present invention may be used in combination with a dye of the same system or a dye of another system, for example, a nitrothiazole dye such as B-106 which can be discharged.

[0018]

Next, the present invention will be described in more detail with reference to examples.
As will be described, the present invention will be described below without departing from the gist thereof.
It is not limited to the embodiment. Example 1 In the above general formula [1], R₁Is a methoxy group, R_TwoBut
Tylsulfonyl group, R _ThreeAnd R_FourAre both methoxyethyl
0.5 g of the azo dye of the present invention
Acid-formaldehyde condensate 0.5g and higher alcohol
Dispersed in 2 L of water containing 0.25 g of sulfuric acid ester
Thus, a dyeing bath was prepared. Polyester fiber
After immersing 100 g of fiber and dyeing at 130 ° C for 60 minutes,
After washing, washing and drying, a blue dyed cloth
Obtained. Furthermore, the following composition on the obtained blue cloth
White with a good blue background after printing and discharging the white paste
A discharge cloth was obtained. White discharge paste composition 10 parts stannous chloride 10 parts tetrocin P-300 3 parts urea 3 parts 12% maple gum 60 60 parts water 24 parts discharge processing
Min) ───> water washing───> reduction washing───> water washing───>
 Drying The dyestuff of Example 1 is 2-amino-6-nitro in 85% phosphoric acid.
Lobenzothiazole is treated with 40% nitrosylsulfuric acid
Zonated, N, N-dimethoxyethyl-2-methoxy-5
-In ice water with methylsulfonylaminoaniline dissolved
In addition to coupling and filtering the generated crystals
More obtained. The dye has a .lambda.max (in acetone) of 585n.
m of blue crystals. Comparative Example 1 Polyester was prepared in the same manner as in Example 1 using B-106.
When the fibers were dyed and evaluated, the results shown in Table 1 were obtained.

The white discharge evaluation is evaluated by gray scale, and the fifth grade is the best and the first grade is the worst.

The washing fastness was measured according to the JIS L0844-1973 A-4 method, and the sublimation fastness was measured according to the JIS L 0879-1968-B method.

[0021]

[Table 1] Structural formula of Comparative Example 2 (described in JP-A-55-80584)

[0022]

Embedded image Comparative Example 1 is clearly inferior in fastness. Comparative Example 2 is slightly inferior in sublimation fastness and dischargeability. Examples 2 to 8 The dyes shown in Table 2 were synthesized according to Example 1, and polyester fibers were dyed in the same manner as in Example 1, and the fastness and discharge properties were examined. Table 2 shows the results.

[0023]

[Table 2] The compound of the present invention is, for example, a polyester fiber which is particularly excellent in white discharge property as compared with this known compound, despite having a very similar structure to the compound known from JP-A-55-80584. It is extremely useful as a dye for use.

Claims (2)

[Claims] [Claim 1] The following general formula [1] (Wherein R ₁ represents a hydrogen atom, a methoxy group or an ethoxy group, R ₂ represents a C ₁ to C ₆ alkylsulfonyl group, and R ₃ and R ₄ are each independently C ₁ to C ₆
Represents an alkyl group, C ₁ -C ₆ -alkoxy-carbonylethyl group, C ₁ -C ₆ -alkoxy-ethyl group, cyanoethyl group or allyl group, provided that at least one of R ₃ and R ₄ is an allyl group Is a water-insoluble monoazo dye represented by the formula: wherein R ₂ may be a C ₁ to C ₆ -alkyl-carbonyl group. 2. A fiber material dyed or printed with the dye according to claim 1.